GB816578A - ª‡:ª‡-diphenyl-ª‰-amino-propanols and process for their manufacture - Google Patents
ª‡:ª‡-diphenyl-ª‰-amino-propanols and process for their manufactureInfo
- Publication number
- GB816578A GB816578A GB30392/55A GB3039255A GB816578A GB 816578 A GB816578 A GB 816578A GB 30392/55 A GB30392/55 A GB 30392/55A GB 3039255 A GB3039255 A GB 3039255A GB 816578 A GB816578 A GB 816578A
- Authority
- GB
- United Kingdom
- Prior art keywords
- phenyl
- piperidino
- diphenyl
- propiophenone
- compounds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000004519 manufacturing process Methods 0.000 title 1
- PWMWNFMRSKOCEY-UHFFFAOYSA-N 1-Phenyl-1,2-ethanediol Chemical compound OCC(O)C1=CC=CC=C1 PWMWNFMRSKOCEY-UHFFFAOYSA-N 0.000 abstract 8
- 235000010290 biphenyl Nutrition 0.000 abstract 5
- 239000004305 biphenyl Substances 0.000 abstract 5
- -1 methoxy, ethoxy Chemical group 0.000 abstract 5
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 abstract 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 abstract 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 abstract 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 229960001484 edetic acid Drugs 0.000 abstract 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 150000002576 ketones Chemical class 0.000 abstract 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 150000003151 propanoic acid esters Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/092—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B22—CASTING; POWDER METALLURGY
- B22D—CASTING OF METALS; CASTING OF OTHER SUBSTANCES BY THE SAME PROCESSES OR DEVICES
- B22D7/00—Casting ingots, e.g. from ferrous metals
- B22D7/06—Ingot moulds or their manufacture
- B22D7/10—Hot tops therefor
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises compounds of the general formula <FORM:0816578/IV (b)/1> in which R1 and R2 are each a hydrogen atom or a halogen atom or a hydroxyl, methyl, methoxy, ethoxy or benzyloxy group, and <FORM:0816578/IV (b)/2> represents a hydrogenated heterocyclic ring, and acid addition salts of these compounds. The compounds are made by the reaction of a phenyl magnesium halide with a phenyl ethyl ketone or a propionic acid ester, substituted in the side chain by a saturated heterocyclic radical, the phenyl radicals being substituted, if required, by halogen atoms or methyl, methoxy or ethoxy groups or benzyloxy groups and, if desired, splitting off the benzyl radical from any benzyloxy group in the product by catalytic hydrogenation. The bases obtained may be connected to their acid addition salts with, for example, hydrochloric, hydrobromic, hydriodic, sulphuric, phosphoric, amidosulphonic, formic, acetic, malonic, succinic, lactic, malic, maleic, citric, benzoic, salicylic, p-aminosalicylic, aceturic, phenol-sulphonic, hydroxyethane-sulphonic or ethylene diamine tetracetic acid. The compounds are used as therapeutic agents. Examples describe the preparation of the 1 : 1 - diphenyl - 2 - piperidino -, 1 - phenyl - 1 - (para - benzyloxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (para - hydroxyphenyl) - 2 - piperidino -, 1 : 1 - diphenyl - 2 - pyrrolidino -, 1 : 1 - diphenyl - 2 - morpholino -, 1 - phenyl - 1 - (4 - chlorophenyl) - 2 - piperidino -, 1 - phenyl - 1 - (3 : 4 - dimethoxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (3 - ethoxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (2 - methoxyphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (3 - methylphenyl) - 2 - piperidino -, 1 - phenyl - 1 - (4 - methoxyphenyl) - 2 - piperidino -, 1 : 1 - diphenyl - 2 - (1 : 2 : 3 : 4) - tetrahydro - isoquinolino - and 1 : 1 - diphenyl - 2 - (a - methyl - piperidino) - propanols. Phenyl ethyl ketones, substituted by a basic group in the a -position, which are used as starting materials, are made by treating a propiophenone with bromine and reacting the product with a heterocyclic base. Specified ketones prepared by this method comprise a -piperidinopropiophenone and the corresponding p-benzyloxy and m-p-dimethoxy derivatives, a -pyrrolidino - propiophenone a - morpholino - propiophenone, a - (1 : 2 : 3 : 4)tetrahydro - isoquinoline - propiophenone and a - (a 1 - methylpiperidino) - propiophenone. Specifications 307,304, 307,307, [both in Class 2 (iii)], and 491,951, [Group IV], are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF15966A DE1021846B (en) | 1954-10-23 | 1954-10-23 | Process for the production of ª ‡, ª ‡ -diphenyl-ª ‰ - (tert -amino) -propanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB816578A true GB816578A (en) | 1959-07-15 |
Family
ID=7088067
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30392/55A Expired GB816578A (en) | 1954-10-23 | 1955-10-24 | ª‡:ª‡-diphenyl-ª‰-amino-propanols and process for their manufacture |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2827460A (en) |
| CH (1) | CH339926A (en) |
| DE (1) | DE1021846B (en) |
| FR (1) | FR1162131A (en) |
| GB (1) | GB816578A (en) |
| NL (2) | NL93401C (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1111208B (en) * | 1957-07-18 | 1961-07-20 | Hoechst Ag | Process for the production of cough-relieving, basic substituted diphenylcarbinol esters |
| US3031377A (en) * | 1957-11-26 | 1962-04-24 | Bayer Ag | 1-omicron-chlorophenyl-1-phenyl-3-dimethyl-amino-propanol-1 antitussive process and compositions |
| US3161646A (en) * | 1959-02-19 | 1964-12-15 | Sterling Drug Inc | 1, 2-bis (substituted phenyl)-3-tertiary-amino-1-propanols |
| DE1164388B (en) * | 1959-03-02 | 1964-03-05 | Temmler Werke | Process and apparatus for the production of aryl alkyl bromoketones |
| US3157656A (en) * | 1960-07-20 | 1964-11-17 | Olin Mathieson | Heterocyclic compounds |
| US3627832A (en) * | 1964-10-16 | 1971-12-14 | Sterling Drug Inc | AMINO-LOWER-ALKOXY-DIBENZO{8 a,d{9 CYCLOHEPTENES AND 5-ALKYL and -ARALKYL DERIVATIVES |
| GB1489989A (en) * | 1974-03-04 | 1977-10-26 | Temmler Ag | Alpha,alpha-diaryl-beta-(tert-amino)-propanols processes for their preparation and pharmaceutical compositions containing them |
| US4361573A (en) * | 1974-03-04 | 1982-11-30 | Temmler Ag | α,α-Diaryl-β-(tert-amino)-propanols and diuretic pharmaceutical compositions containing them |
| US4329367A (en) * | 1974-08-05 | 1982-05-11 | Ciba-Geigy Corporation | 1-(Aralkoxyphenyl)-2-(bis-arylalkylamino)-alkanes |
| US4069256A (en) * | 1975-01-20 | 1978-01-17 | Sterling Drug Inc. | Anti-inflammatory phenyl-lower-alkylamines |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE675817C (en) * | 1935-12-07 | 1939-05-17 | Albert Ag Chem Werke | Process for the preparation of readily water-soluble salts of diarylaminoalkylcarbinoln |
| DE694005C (en) * | 1938-07-20 | 1940-07-23 | Albert Ag Chem Werke | Disinfectants |
| DE713257C (en) * | 1939-05-18 | 1941-11-04 | Albert Ag Chem Werke | Disinfectants |
-
0
- NL NL201277D patent/NL201277A/xx unknown
- NL NL93401D patent/NL93401C/xx active
-
1954
- 1954-10-23 DE DEF15966A patent/DE1021846B/en active Pending
-
1955
- 1955-10-17 US US541086A patent/US2827460A/en not_active Expired - Lifetime
- 1955-10-21 FR FR1162131D patent/FR1162131A/en not_active Expired
- 1955-10-21 CH CH339926D patent/CH339926A/en unknown
- 1955-10-24 GB GB30392/55A patent/GB816578A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| CH339926A (en) | 1959-07-31 |
| NL201277A (en) | |
| US2827460A (en) | 1958-03-18 |
| DE1021846B (en) | 1958-01-02 |
| FR1162131A (en) | 1958-09-09 |
| NL93401C (en) |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB816578A (en) | ª‡:ª‡-diphenyl-ª‰-amino-propanols and process for their manufacture | |
| ES443725A1 (en) | METHOD TO PRODUCE A HYPOTENSOR PRODUCT. | |
| ES8507498A1 (en) | A PROCEDURE FOR THE PREPARATION OF PHENYLQUINOLIN-CARBOXYLIC ACIDS. | |
| ES417333A1 (en) | Omega-(4'-(3"-indolyl)-piperidino)-alkyl-arylketones | |
| Pollard et al. | Derivatives of piperazine. XXIV. Synthesis of 1-arylpiperazines and amino alcohol derivatives | |
| CH634569A5 (en) | METHOD FOR PRODUCING MORPHOLINE DERIVATIVES. | |
| DE3854109D1 (en) | METHOD FOR PRODUCING CHINOLINE CARBONIC ACIDS. | |
| ES391633A1 (en) | 2,2,-diaryl-4-4-aryl-4-hydroxy-piperidino butyramides | |
| ATE3028T1 (en) | CYCLOPENTENONE AND CYCLOPENTENOL DERIVATIVES AND PROCESS FOR THEIR PRODUCTION. | |
| US3418355A (en) | Didecyl quaternary ammonium compounds | |
| ES409237A1 (en) | Process for the preparation of 3-benzoylphenyl alkanoic acids | |
| US3163649A (en) | Substituteb phenyl-piperazine | |
| GB872997A (en) | Substituted ún-aminoalkoxy-acyl benzenes and processes for their manufacture | |
| ES388953A1 (en) | 3- 3,4, - dichloro -6,- alkylphenyl - delta2 - pyrazoline deriva tives and a process for their manufacture | |
| ES8201526A1 (en) | 1,1'-Biphenyl-2-yl alkylamine derivatives, their production and cardiovascular preparations containing same. | |
| Lagemann et al. | Ultrasonic Velocity in a Series of Alkyl Acetates | |
| GB698253A (en) | Improvements in or relating to pyrazoline sulphonic acids | |
| US2655503A (en) | Quaternary salts of y-stilbazolines | |
| ES227224A1 (en) | A PROCEDURE FOR THE OBTAINING OF SYNTHETIC PRODUCTS THAT HAVE FUNGICIDE ACTIVITY. | |
| GB891862A (en) | New piperidine derivatives and processes for preparing the same | |
| ES355003A2 (en) | PROCEDURE FOR THE PREPARATION OF NEW AMINO-KETONES. | |
| GB1474906A (en) | Pyrolidine derivatives | |
| ES311604A1 (en) | A procedure for the preparation of benzodiazepine derivatives. (Machine-translation by Google Translate, not legally binding) | |
| ES428011A1 (en) | PROCEDURE FOR THE PREPARATION OF 2-AMINO-3,5-DIBROMO-BENZYLAMINE. | |
| ES222686A1 (en) | A PROCEDURE FOR OBTAINING BENZOIC ACID DERIVATIVES |